Silybin BCAS# 142797-34-0 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 142797-34-0 | SDF | Download SDF |
| PubChem ID | 1548994 | Appearance | White powder |
| Formula | C25H22O10 | M.Wt | 482.44 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Synonyms | Legalon; Flavobion;65666-07-1 | ||
| Solubility | Soluble in acetone, ethanol, ethyl acetate and methanol; insoluble in water | ||
| Chemical Name | (2R,3R)-3,5,7-trihydroxy-2-[(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one | ||
| SMILES | COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O | ||
| Standard InChIKey | SEBFKMXJBCUCAI-WAABAYLZSA-N | ||
| Standard InChI | InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23-,24-,25+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Silybin B and silybin A show strong effects on cell growth inhibition and apoptosis induction in human chronic myeloid leukemia K562 cells. 2. Silybin B exhibits 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity. 3. Silybin B and silybin A are potent inhibitors of both raloxifene 4'- and 6-glucuronidation in all enzyme systems. |
| Targets | Calcium Channel | ROS |
Silybin B Dilution Calculator
Silybin B Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.0728 mL | 10.364 mL | 20.728 mL | 41.4559 mL | 51.8199 mL |
| 5 mM | 0.4146 mL | 2.0728 mL | 4.1456 mL | 8.2912 mL | 10.364 mL |
| 10 mM | 0.2073 mL | 1.0364 mL | 2.0728 mL | 4.1456 mL | 5.182 mL |
| 50 mM | 0.0415 mL | 0.2073 mL | 0.4146 mL | 0.8291 mL | 1.0364 mL |
| 100 mM | 0.0207 mL | 0.1036 mL | 0.2073 mL | 0.4146 mL | 0.5182 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Bax/Tubulin/Epithelial-Mesenchymal Pathways Determine the Efficacy of Silybin Analog HM015k in Colorectal Cancer Cell Growth and Metastasis.[Pubmed:29875662]
Front Pharmacol. 2018 May 23;9:520.
The inhibition of apoptosis, disruption of cellular microtubule dynamics, and over-activation of the epithelial mesenchymal transition (EMT), are involved in the progression, metastasis, and resistance of colorectal cancer (CRC) to chemotherapy. Therefore, the design of a molecule that can target these pathways could be an effective strategy to reverse CRC progression and metastasis. In this study, twelve novel silybin derivatives, HM015a-HM015k (15a-15k) and compound 17, were screened for cytotoxicity in CRC cell lines. Compounds HM015j and HM015k (15k and 15j) significantly decreased cell proliferation, inhibited colony formation, and produced cell cycle arrest in CRC cells. Furthermore, 15k significantly induced the formation of reactive oxygen species and apoptosis. It induced the cleavage of the intrinsic apoptotic protein (Bax p21) to its more efficacious fragment, p18. Compound 15k also inhibited tubulin expression and disrupted its structure. Compound 15k significantly decreased metastatic LOVO cell migration and invasion. Furthermore, 15k reversed mesenchymal morphology in HCT116 and LOVO cells. Additionally, 15k significantly inhibited the expression of the mesenchymal marker N-cadherin and upregulated the expression of the epithelial marker, E-cadherin. Compound 15k inhibited the expression of key proteins known to induce EMT (i.e., DVL3, beta-catenin, c-Myc) and upregulated the anti-metastatic protein, cyclin B1. Overall, in vitro, 15k significantly inhibited CRC progression and metastasis by inhibiting apoptosis, tubulin activity and the EMT pathways. Overall, these data suggest that compound 15k should be tested in vivo in a CRC animal model for further development.
Inhibitory effects of silybin on the efflux pump of methicillinresistant Staphylococcus aureus.[Pubmed:29845191]
Mol Med Rep. 2018 Jul;18(1):827-833.
Bacterial multidrug resistance efflux systems serve an important role in antimicrobial resistance. Thus, identifying novel and effective efflux pump inhibitors that are safe with no adverse side effects is urgently required. Silybin is a flavonolignan component of the extract from the milk thistle seed. To order to investigate the mechanism by which silybin inhibits the efflux system of methicillinresistant Staphylococcus aureus (MRSA), antimicrobial susceptibility testing and the doubleplate method were used to evaluate the effect of silybin on MRSA41577. The ability of silybin to inhibit the efflux of ciprofloxacin from MRSA was evaluated by performing a fluorescence assay. Reverse transcriptionquantitative polymerase chain reaction analysis revealed that silybin reduced the expression of the quinolone resistance protein NorA (norA) and quaternary ammonium resistance proteins A/B (qacA/B) efflux genes in MRSA. This suggested that silybin may effectively inhibit the efflux system of MRSA41577. Compared with the control, MRSA41577 treated with silybin for 16 h exhibited a 36 and 49% reduction in the expression of norA and qacA/B, respectively. Inhibition of the expression of these genes by silybin restored the sensitivity of MRSA41577 to antibiotics, indicating that efflux pump inhibitors, which act by inhibiting the efflux system of MRSA, may disrupt the MRSA resistance to antibiotics, rendering the bacteria sensitive to these drugs.
A comparison of the diastereoisomers, silybin A and silybin B, on the induction of apoptosis in K562 cells.[Pubmed:22224281]
Nat Prod Commun. 2011 Nov;6(11):1653-6.
Two diastereoisomers of silybin, silybin A and Silybin B, were separated from silymarin by HPLC in our previous study. The present study assessed the effects of the diastereoisomers on cell apoptosis, and compared these with their mixture, silybin, in human chronic myeloid leukemia K562 cells. Both isomers showed stronger effects on cell growth inhibition and apoptosis induction than silybin. Compared with Silybin B, silybin A showed higher effects on the production of intracellular reactive oxygen species and Ca2+. These results suggest that silybin A and Silybin B have similar potency on apoptosis induction with different oxidative effects. Antagonistic effects may exist between silybin A and Silybin B, partially through ROS production and Ca2+ increase.
Milk Thistle Constituents Inhibit Raloxifene Intestinal Glucuronidation: A Potential Clinically Relevant Natural Product-Drug Interaction.[Pubmed:26070840]
Drug Metab Dispos. 2015 Sep;43(9):1353-9.
Women at high risk of developing breast cancer are prescribed selective estrogen response modulators, including raloxifene, as chemoprevention. Patients often seek complementary and alternative treatment modalities, including herbal products, to supplement prescribed medications. Milk thistle preparations, including silibinin and silymarin, are top-selling herbal products that may be consumed by women taking raloxifene, which undergoes extensive first-pass glucuronidation in the intestine. Key constituents in milk thistle, flavonolignans, were previously shown to be potent inhibitors of intestinal UDP-glucuronosyl transferases (UGTs), with IC50s Silybin B were potent inhibitors of both raloxifene 4'- and 6-glucuronidation in all enzyme systems. The Kis (human intestinal microsomes, 27-66 microM; UGT1A1, 3.2-8.3 microM; UGT1A8, 19-73 microM; and UGT1A10, 65-120 microM) encompassed reported intestinal tissue concentrations (20-310 microM), prompting prediction of clinical interaction risk using a mechanistic static model. Silibinin and silymarin were predicted to increase raloxifene systemic exposure by 4- to 5-fold, indicating high interaction risk that merits further evaluation. This systematic investigation of the potential interaction between a widely used herbal product and chemopreventive agent underscores the importance of understanding natural product-drug interactions in the context of cancer prevention.
